Ethylenediamine is a composition well known in the industry and is used in a wide variety of applications. These applications for ethylenediamine include utility as chelating agents and surfactants, fabric softeners, lubricating oil additives, rubber accelerators, fungicides, insecticides, synthetic waxes, asphalt wetting agents and resinous polymers. In view of the wide utility of ethylenediamine, there has been substantial work done in the preparation of ethylenediamine which involves the reaction of ethylene oxide with ammonia, monoethanolamines with ammonia, or ethylene glycol with ammonia. The processes are catalytic and objectives of the processes have been to maximize conversion of the organic substrate with ammonia to form ethylenediamine and to maximize selectivity. Another approach to the preparation of ethylenediamine has involved the reaction of ethylene dichloride with ammonia but such process has numerous drawbacks because of the production of by-product sodium chloride and also because of the cost of corrosion-resistant equipment for such process.
Representative art showing the manufacture of ethylenediamine as well as other amines is shown on the following U.S. patents:
U.S. No. 3,068,290 discloses a process producing ethylenediamine by reacting monoethanolamine or ethylene oxide in the presence of catalysts, which by and large are hydrogenation catalysts such as Raney nickel, cobalt, reduced nickels, copper chromite, platinimum, osmium, palladium and the like either alone or on a supporting medium. Such catalysts have been combined with alkaline earth metal oxides such as magnesium oxide which enhance activity and increase selectivity.
U.S. No. 3,137,370 discloses the manufacture of ethylenediamine utilizing a hydrogenation catalyst comprising nickel and copper with the reaction carried out in the presence of water.
U.S. No. 3,766,184 discloses the preparation of ethylenediamine by reacting monoethanolamine and ammonia in the presence of an amination catalyst comprising iron, nickel or cobalt.
U.S. No. 4,123,462 discloses amination processes using nickel-rhenium catalysts as the catalyst.
Catalytic processes have been used for the manufacture of alkylamines and diamines such as methylamines, ethylamines and, and general C.sub.1 to C.sub.6 alkylamines. Representative patents show the amination of alkanols to produce alkylamines including methylamines, etc. as set forth in the following patents:
U.S. No. 4,458,092 cites a number of patents which disclose processes for the manufacture of amines by the reaction of alcohol and ammonia in the presence of zeolites. The zeolites used in this patent for producing methylamines in high selectivity were rare earth Y zeolite and hydrogen exchanged Y zeolite.
U.S. No. 4,436,938 discloses a process for producing methylamines by reacting methanol or dimethylether with ammonia over a binderless zeolite A catalyst. The zeolite being exchanged with various cations such as sodium, calcium, magnesium, cerium and lanthanum.
U.S. No. 4,434,300 discloses a process for producing methylamines by reacting methanol with ammonia using macroporous highly acidic alumino-silicates. Microporous hydrogen-chabazite-erionite was the preferred catalyst.
U.S. No. 4,254,061 discloses a catalytic process for producing monomethylamine by reacting methanol and ammonia over a catalyst selected from the group of mordenite, ferrierite, erionite, and clinoptilolite. Specific cations are suggested for each zeolite system.
U.S. No. 4,205,012 discloses the manufacture of amines by reacting an alcohol with ammonia in the presence of a zeolite and particularly the zeolite designated FU-1. The catalytic process produces mono and dimethylamine in preference to trimethylamine.